Syncing Outlook mail with Apple Mail 10.4.x

30 October, 2007 – 6:41 am

It’s a real pain for Apple users to synchronize Microsoft Outlook with Apple Mail, but Parallels (or VMWare) brings us one step closer. You can virtualize your work environment (typically a PC with Outlook/Exchange access) and host your own local IMAP server, to sync mail between your virtual PC and say your MacBookPro. The concept is, for each client I might work for, I run a virtual PC that has all their security/access requirements catered for. Since the majority of clients I work for use some version of XP with Outlook Exchange, I decided to host a single IMAP server locally that these virtual PCs can then synchronize with. That way I can continue to use my mac offline, and get the other benefits of time management apps like GTD Inbox.

Following are some less than trivial installation instructions pieced together from an article here and more help on the subject here. These installations are suitable for Mac OSX (10.4.x)

1. Get a copy of the latest source for UW-IMAP here:
ftp://ftp.cac.washington.edu/imap/imap.tar.Z

2. tar xfz imap.tar.Z

3. cd imap-2006k.DEV.SNAP-0710261815

4. In order to avoid 0×800CCCDD errors (lost mailbox lock) when using Outlook make sure you compile with the MICROSOFT_BRAIN_DAMAGE (MSBD) flag which effectively disables IDLE.
perl -pi -e 's/^#(MSBD)/$1/' src/imapd/Makefile

5. Make a directory to store your IMAP mailboxes.
sudo mkdir -p ~koops/Library/Mail/IMAP

6. Change ownership and permissions, make sure you use a username that exists.
sudo chmod go-rx ~koops/Library/Mail/IMAP
sudo chown koops ~koops/Library/Mail/IMAP

7. Edit the default mail subdirectory to the directory location created before.
perl -pi -e 's/mailsubdir\s\=\sNIL/mailsubdir \= \"Library\/Mail\/IMAP\"/' src/osdep/unix/env_unix.c

8. Compile the code using make with oxp parameter.
sudo make oxp PASSWDTYPE=pam SSLTYPE=unix

9. Make an imapd directory in your libexec folder (make sure it exists first).
sudo mkdir /usr/local/libexec/impapd

10. Copy the relevant binaries to that location.
sudo cp imapd/imapd /usr/local/libexec/imapd

11. Copy the following files to the following locations.
sudo cp /etc/pam.d/login /etc/pam.d/imap
sudo cp /etc/pam.d/login /etc/pam.d/imaps

12. Create a new plist in LaunchDaemons then edit it in vi
sudo touch /Library/LaunchDaemons/imap3.plist
sudo vi /Library/LaunchDaemons/imap3.plist
You need to add something like this to the plist

<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple Computer//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
<dict>
<key>Label</key>
<string>edu.washington.imapd</string>
<key>ProgramArguments</key>
<array>
<string>/usr/local/libexec/imapd</string>
</array>
<key>OnDemand</key>
<true/>
<key>Sockets</key>
<dict>
<key>Listeners</key>
<dict>
<key>Bonjour</key>
<false/>
<key>SockServiceName</key>
<string>imap</string>
<key>SockType</key>
<string>stream</string>
</dict>
</dict>
<key>inetdCompatibility</key>
<dict>
<key>Wait</key>
<false/>
</dict>
</dict>
</plist>


13. Launch the imap server
sudo launchctl load /Library/LaunchDaemons/imap3.plist

14. Test connectivity

telnet localhost 143
Trying ::1...
Connected to localhost.
Escape character is '^]'.
* OK [CAPABILITY IMAP4REV1 LITERAL+ SASL-IR LOGIN-REFERRALS STARTTLS] localhost IMAP4rev1 2006k.397 at Mon, 29 Oct 2007 12:36:34 +1100 (EST)
. logout
* BYE 90kts-mac.local IMAP4rev1 server terminating connection
. OK LOGOUT completed


Now you can add the IMAP server to your Mail app and create custom folders which you can then sync from your virtual PCs.